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Cheap flights from Canada to Chicago from C$ 162

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
YYZ — CHI
2 Apr — 9 Apr1
1 adult
Tue 2/4
Tue 9/4

How far in advance should I book a flight from Canada to Chicago?

Users have found that booking a flight from Canada to Chicago at least 27 days early can save you up to 78% on average compared to booking a flight this week. If booking 27 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 488 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 663 for flights departing within the next 3 days.

What is the cheapest month to fly from Canada to Chicago?

Flights from Canada to Chicago lean towards being more expensive in July. Prices are generally better when you fly from Canada to Chicago in January, with the cheapest ticket starting at C$ 242.

When is the cheapest time to fly from Canada to Chicago (CA - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.

Cheap Air Canada flights from Canada to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Canada and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
Take a peek at the cheapest Air Canada flights we've detected travelling from Canada to Chicago. Make sure to check back often as deals are often changing.
Thu 25/48:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Thu 2/56:00 a.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 28/3C$ 303
Sat 4/54:00 p.m.YYZ - ORD
1 stop5h 16mAir Canada
Mon 6/56:00 a.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 27/3C$ 322
Tue 30/46:15 a.m.YUL - ORD
Nonstop2h 46mAir Canada
Tue 7/56:00 a.m.ORD - YUL
1 stop5h 18mAir Canada
Deal found 26/3C$ 325
Sat 4/510:10 a.m.YUL - ORD
1 stop5h 44mAir Canada
Sun 5/56:00 a.m.ORD - YUL
1 stop6h 18mAir Canada
Deal found 27/3C$ 330
Thu 23/57:50 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Tue 28/54:00 p.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 26/3C$ 337
Tue 2/79:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sat 6/79:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 27/3C$ 340
Wed 3/46:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Wed 10/49:40 a.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 27/3C$ 470
Sat 6/47:59 a.m.YYZ - ORD
Nonstop1h 59mAir Canada
Tue 9/44:35 p.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 27/3C$ 488
Wed 3/46:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 7/49:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 27/3C$ 497

Cheap WestJet flights from Canada to Chicago

Explore cheap flight options specifically provided by WestJet for the route between Canada and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
To aid your search, here are some of the cheapest WestJet flights we've found from Canada to Chicago. Deals are refreshing constantly so come back soon for more options.
Fri 6/912:30 p.m.YYC - ORD
Nonstop3h 27mWestJet
Tue 10/95:35 p.m.ORD - YYC
Nonstop3h 39mWestJet
Deal found 27/3C$ 433
Thu 18/41:20 p.m.YYZ - ORD
1 stop11h 32mWestJet
Sun 21/47:05 a.m.ORD - YYZ
1 stop14h 41mWestJet
Deal found 27/3C$ 443
Thu 6/66:04 p.m.YYZ - ORD
1 stop6h 51mWestJet
Sat 8/65:45 p.m.ORD - YYZ
1 stop4h 05mWestJet
Deal found 27/3C$ 446
Thu 4/46:00 a.m.YYZ - ORD
1 stop4h 31mWestJet
Sun 21/46:20 a.m.ORD - YYZ
1 stop4h 11mWestJet
Deal found 26/3C$ 526
Thu 4/46:00 a.m.YYZ - ORD
1 stop4h 31mWestJet
Sun 7/49:00 a.m.ORD - YYZ
1 stop8h 59mWestJet
Deal found 28/3C$ 567
Thu 4/46:30 a.m.YYZ - MDW
1 stop5h 17mWestJet
Sun 7/46:19 a.m.MDW - YYZ
1 stop15h 41mWestJet
Deal found 28/3C$ 572

Cheap Canada to Chicago flights in March & April 2024

Find cheap flight options from Canada to Chicago specifically for the months of March and April 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 586,909 searches. Prices were last updated on 28 March 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. For more flight deals, be sure to check back very soon.
Thu 25/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 2/55:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 277
Wed 17/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 279
Tue 23/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 281
Tue 23/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 287
Wed 24/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 28/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 288
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 18/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 289
Fri 19/44:45 p.m.YUL - MDW
1 stop5h 52mPorter Airlines
Mon 22/48:00 a.m.MDW - YUL
1 stop4h 45mPorter Airlines
Deal found 27/3C$ 289
Tue 23/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 27/412:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 28/3C$ 291
Fri 26/46:35 p.m.YUL - MDW
1 stop4h 02mPorter Airlines
Tue 30/48:00 a.m.MDW - YUL
1 stop4h 45mPorter Airlines
Deal found 26/3C$ 291

Canada to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Canada and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. For more flight deals, be sure to check back very soon.
Thu 25/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 2/55:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 277
Wed 17/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 279
Tue 23/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 281
Tue 7/59:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 10/58:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 284
Tue 23/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 287
Wed 24/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 28/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 288
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 18/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 289
Fri 19/44:45 p.m.YUL - MDW
1 stop5h 52mPorter Airlines
Mon 22/48:00 a.m.MDW - YUL
1 stop4h 45mPorter Airlines
Deal found 27/3C$ 289
Tue 23/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 27/412:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 28/3C$ 291

Direct flights to Chicago from Canada

Discover non-stop flight options from Canada to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
For a quicker trip, book one of these direct flights from Canada to Chicago. Users can also choose from other Canada to Chicago flights by using the search form above.
Thu 25/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 2/55:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 277
Wed 17/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 279
Tue 23/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 281
Tue 7/59:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 10/58:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 284
Tue 23/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 30/45:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 287
Wed 24/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 28/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 288
Wed 17/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 18/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 289
Tue 23/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 27/412:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 28/3C$ 291
Thu 6/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 11/68:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 294

Canada to Chicago flights leaving soon

Find last-minute flight options from Canada to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
Users seeking a last-minute flight from Canada to Chicago should consider booking one of these fares. Users should examine the flight details to ensure there are no surprises.
Sat 6/410:45 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 17/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 363
Thu 11/412:50 p.m.YUL - MDW
1 stop4h 27mPorter Airlines
Sun 21/48:40 a.m.MDW - YUL
1 stop4h 20mPorter Airlines
Deal found 27/3C$ 379
Wed 10/42:10 p.m.YYC - ORD
1 stop9h 49mDelta
Wed 17/412:15 p.m.ORD - YYC
1 stop9h 41mDelta
Deal found 27/3C$ 385
Sun 7/48:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 13/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 385
Sun 7/410:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 13/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 28/3C$ 386
Sat 6/411:55 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Wed 17/41:20 p.m.ORD - YYZ
1 stop8h 00mAmerican Airlines
Deal found 27/3C$ 395
Wed 3/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 10/48:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 412
Sat 6/411:51 a.m.YYZ - ORD
1 stop7h 26mAmerican Airlines
Wed 17/412:20 p.m.ORD - YYZ
1 stop9h 00mAmerican Airlines
Deal found 27/3C$ 413
Thu 4/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 21/48:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 26/3C$ 417

One-way flights to Chicago from Canada

Search for one-way flight options from Canada to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
Some of the best available deals we've found on one-way flights from Canada to Chicago. Those needing a return flight from Canada to Chicago can use the search form above.
Wed 1/59:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 26/3C$ 162
Tue 7/59:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 27/3C$ 168
Sat 15/66:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 26/3C$ 171
Sat 27/46:15 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 27/3C$ 173
Wed 24/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 27/3C$ 175
Wed 1/53:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 28/3C$ 177
Sun 26/53:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 27/3C$ 178
Wed 1/57:00 a.m.YUL - MDW
1 stop4h 07mPorter Airlines
Deal found 27/3C$ 178
Wed 5/69:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 28/3C$ 182

Find flights from Canada to Chicago within your budget

Customize your flight search to find flights from Canada to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 277 - C$ 489

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/4

Nonstop1h 47m

Chicago Midway

Thu 2/5

Nonstop1h 42m

C$ 277

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 25/4

Nonstop1h 54m

Chicago O'Hare Intl

Thu 2/5

Nonstop1h 45m

C$ 303

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 17/4

Nonstop1h 55m

Chicago O'Hare Intl

Wed 24/4

Nonstop1h 40m

C$ 304

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 7/5

Nonstop1h 54m

Chicago O'Hare Intl

Tue 14/5

Nonstop1h 43m

C$ 310

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/7

Nonstop1h 54m

Chicago O'Hare Intl

Sun 7/7

Nonstop1h 48m

C$ 338

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 17/4

1 stop6h 09m

Chicago O'Hare Intl

Sat 20/4

1 stop8h 11m

C$ 345

Vancouver IntlChicago O'Hare Intl

YVR - ORD

YVRORD

Vancouver Intl

Wed 24/4

1 stop11h 11m

Chicago O'Hare Intl

Wed 1/5

1 stop8h 38m

C$ 432

CalgaryChicago O'Hare Intl

YYC - ORD

YYCORD

Calgary

Fri 6/9

Nonstop3h 27m

Chicago O'Hare Intl

Tue 10/9

Nonstop3h 39m

C$ 433

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 3/5

1 stop7h 05m

Chicago O'Hare Intl

Mon 6/5

2 stops12h 49m

C$ 489

Flights are sorted by cheapest first

Deals found on 26/3

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 28 March 2024.
See what other customers who have flown with Air Canada, WestJet and United Airlines from Canada to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

8.1
Very good
9,157 reviews
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

8.1
Very good
11,437 reviews
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

7.7
Good
2,757 reviews
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

7.5
Good
3,035 reviews
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

7.3
Good
448 reviews
8.1
Very good
9,157 reviews

Overall

8.1

Food

7.3

Crew

8.6

Boarding

8.2

Entertainment

7.4

Comfort

7.9

Reviews

1 / 10

I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose

Related info for your journey

Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • Can I find flights from Canada to Chicago for under C$ 300 on Cheapflights?

    Yes, there are multiple flights from Canada to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 277, but on average you can expect to pay C$ 291.

  • Are there direct flights from Canada to Chicago for under C$ 300 on Cheapflights?

    Cheapflights has 20 direct flights from Canada to Chicago under C$ 300. A good price for a direct flight from Canada to Chicago is less than C$ 295.

  • Are there last-minute flights available from Canada to Chicago for under C$ 400?

    There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than C$ 400.

  • What days are direct flights available from Canada to Chicago?

    You can find direct flights on the following days: Sunday, Monday, Tuesday, Friday, Saturday.

  • How many flights depart from Canada to Chicago on average per day?

    38 flight departures from Canada to Chicago per day on average.
    Early Morning (Midnight to 6am) - 11% of flight departures
    Morning (6am - Midday) - 29% of flight departures
    Afternoon (Noon - 6pm) - 42% of flight departures
    Evening (6pm - Midnight) - 18% of flight departures

  • How long is the flight from Canada to Chicago?

    A quick flight from Canada to Chicago can take about 1h 47m. Porter Airlines provides one of the quickest options available for as low as C$ 277. Canada and Chicago are separated by a distance of 703 km. Most flights are nonstop.

  • What are the cheapest airlines to fly from Canada to Chicago one-way?

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at C$ 162. Air Canada flights start at C$ 183 while deals on American Airlines start at C$ 185 one-way.

  • What are the most popular routes from Canada to Chicago?

  • What are the most popular airlines that fly from Canada to Chicago?

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: Lufthansa (100%), Republic Airways (97%), Copa Airlines( 95%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 212. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 326 on average our data indicates C$ 1,374 when flying from Canada to Chicago.

  • What does YYZ to ORD mean?

    This is defined as Toronto Pearson Intl Airport (YYZ) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Canada to Chicago that include extra baggage allowance?

    The amount of baggage you can bring depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Canada to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Canada to Chicago that include hotel bookings?

    Yes. In addition to deals on Canada to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to see available direct flights.

  • Can I find deals for business class flights from Canada to Chicago?

    Yes. Cheapflights offers flight deals from Canada to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Canada to Chicago that allow pets onboard?

    Many airlines do offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • How recently were the Canada to Chicago flight deals updated?

    The Canada to Chicago flight deals you see on this page were last updated on 28/3.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 10 airlines flying from Canada to Chicago

Discover the top 10 airlines that operate flights from Canada to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 586,909 searches. Data last updated 28 March 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 250AverageC$ 443FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 260AverageC$ 606FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 265AverageC$ 635FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 290AverageC$ 604FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air New ZealandCheapestC$ 298AverageC$ 327FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
DeltaCheapestC$ 317AverageC$ 542FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
ANACheapestC$ 322AverageC$ 437FlexibilityNo cancel feeOn-time80%
Search ANA flights
American AirlinesCheapestC$ 326AverageC$ 623FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Alaska AirlinesCheapestC$ 328AverageC$ 605FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
Endeavor AirlinesCheapestC$ 459AverageC$ 772FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights

Search flights from Canada to Chicago by cabin class

Find flights from Canada to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Classfrom C$ 725/person
Business Classfrom C$ 442/person
Prem Econ Classfrom C$ 543/person
Economy Classfrom C$ 162/person

Hourly flight availability from Canada to Chicago

Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 March 2024.
23%of flight departuresEarly morningMidnight to 6 am
32%of flight departuresMorning6 am to noon
41%of flight departuresAfternoonNoon to 6 pm
4%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Canada to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Canada shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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Can I find deals on last-minute flights from Canada to Chicago?

Yes, you can often find last-minute deals on Canada to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

How can I compare prices from different travel booking sites for flights from Canada to Chicago?

Cheapflights aggregates prices from various travel booking sites. This allows you to compare prices and choose the best deal.

Can I find deals for flights from Canada to Chicago that offer flexible cancellation policies?

Cancellation policies vary by airline and fare type. After entering your flight details, you can view the cancellation policies for each deal in the search results. Some deals may offer flexibility in terms of cancellation and changes.

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